title: Microbial transformation of (+)-nootkatone and the antiproliferative activity of its metabolites.
abstract: Six metabolites were obtained as a result of microbial transformation of (+)-nootkatone (1) by the fungal strains: Botrytis, Didymosphaeria, Aspergillus, Chaetomium and Fusarium. Their structure were established as (+)-(4R,5S,7R,9R)-9α-hydroxynootkatone (2), (+)-(4R,5S,7R)-13-hydroxynootkatone (3) and (+)-(4R,5S,7R,9R,11S)-11,12-epoxy-9α-hydroxynootkatone (4), (+)-(4R,5S,7R,11S)-11,12-epoksynootkatone (5), (+)-(4R,5S,7R)-11,12-dihydroxynootkatone (6) and (+)-(4R,5S,7R)-7,11,12-trihydroxynootkatone (7) on the basis of their spectral data. Two products: (4) and (7) were not previously reported in the literature. The antiproliferative activity of (+)-nootkatone (1) and isolated metabolites (2-7) of its biotransformation has been evaluated.
authors.affiliation: Department of Chemistry, Wroclaw University of Environmental and Life Sciences, Norwida 25, 50-375 Wroclaw, Poland. anna.gliszczynska@wp.pl
authors.forename: Anna
authors.initials: A
authors.lastname: Gliszczyńska
authors.forename: Agnieszka
authors.initials: A
authors.lastname: Łysek
authors.forename: Tomasz
authors.initials: T
authors.lastname: Janeczko
authors.forename: Marta
authors.initials: M
authors.lastname: Świtalska
authors.forename: Joanna
authors.initials: J
authors.lastname: Wietrzyk
authors.forename: Czesław
authors.initials: C
authors.lastname: Wawrzeńczyk
mesh_terms: D000230:Adenocarcinoma / Q000188:drug therapy / Q000473:pathology; D000077192:Adenocarcinoma of Lung; D000970:Antineoplastic Agents / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology*; D001711:Biotransformation; D048708:Cell Growth Processes / Q000187:drug effects; D045744:Cell Line, Tumor; D005658:Fungi / Q000378:metabolism*; D018922:HL-60 Cells; D006801:Humans; D008175:Lung Neoplasms / Q000188:drug therapy / Q000473:pathology; D008968:Molecular Conformation; D015394:Molecular Structure; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C050302:nootkatone